Process for the preparation of 4-amino-beta-phenyl-anthraquinone by amination



Patented Dec. 30, 1230 Arnie PHILIP H. GROGGINS, OF WASHINGTON, DISTRICT OF COLUMBIA No Drawing.

Application filed August 8, 1929. Serial No. 384,516.

(GRANTED UNDER THE AGT 0F MARCH 3, 1883, AS AMENDED APRIL 30, 1928; 370 0. G. 757) QAn HNH The replacement is accomplished by heating with ammonia under pressure. I have found that the addition of definite amounts of nitrobenzene, copper, and its salts serve as catalysts and accelerate the reaction.

When in a pure state, 4-amino-betaphenyl-anthraquinone is obtained as bright red lustrous needle crystals. It melts at 2215-2220 C. It is readily soluble in chlorobenzene, dichlorobenzene and strong sulfuric acid. It gives all the usual characteristic reactions of anthraquinone derivatives of this class. IVith acids it forms the characteristic amino salts which are only slightly soluble 49 in boiling water.

Without limiting my invention to any particular procedure, the following examples in which parts by weight are given, illustrate the application of my invention in the preferred form.

Example ].Twenty parts of 4 (hlg) beta-phenyl-anthraquinone are mixed with 250 parts of 29 per cent ammonia, 10 parts of nitrobenzene, and 1 part cuprous chloride as catalyst. The mixture is then heated at 220 C C. for 4C hours in a pressure autoclave provided with an agitator. The ammonia and nitrobenzene are then removed by distilling with steam. The amino compound is then obtained by filtering. It can be purified by recrystallizing from ortho-dichlorobenzene.

Ea rmzple [[.Twenty parts of -chlorobeta-phenyl-anthraquinone are mixed with 250 parts of ammonia, 0.5 parts cuprous chloride and 1.0 part of copper. The charge is heated in a pressure autoclave provided with an agitator for 24 hours at 240 C. The red amino compound is obtained by filtering ofi the ammoniacal solution.

I am aware that numerous details of the process may be varied through a wide range without departing from the spirit of this in-, vention, and I do not desire limiting the patent granted hereon otherwise than as necessitated by the prior art.

I claim as my invention 1. The process of preparing et-amino-betaphenyl-anthraquinone, which comprises heating 4-halogen-beta-phenyl-anthraquinone with aqueous ammonia under pressure.

2. The process of preparing e-amino-betaphenyl-anthraquinone, which comprises heating 4c-halogen-beta-phenyl-anthraquinone with ammonia under pressure in the presence of nitrobenzene.

3. The process of preparing i-amino-betaphenyl-anthraquinone, which comprises heating -halogeirbeta-phenyl-anthraquinone with aqueous ammonia under pressure in the presence 03": a mixture of metallic copper and its cuprous salts.

4. The process of preparing i-amino-betaphenyl-anthroquinone which comprises heating i-chloro-beta-phenyl-anthraquinone with aqueous ammonia in the presence of LII nitrobenzene and a copper catalyst and then precipitating the amino compound by cooling the ammoniacal solution.

5. As a new article of manufacture 4:- amino beta -pheny1- anthraquinone 11 aw i 11 g most probably the following chemical fornude.

In testimony whereof I have hereunto subscrlbed my name.

PHILIP H. GROGGINS. 

